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Ponoʻoe eʻike e pili ana i nā Pyridines

Ponoʻoe eʻike e pili ana i nā Pyridines

Ponoʻoe eʻike Kūpū

ʻO Pyridine ka mea kumu heterocyclic ka pūpū o keʻano azine. Loaʻa ka Pyridine mai ke benzene ma o ka paniʻana o ka CH i ka N-atom. ʻO keʻano o ka Pyridine e like me ka hanana o benzene, no ka mea, pili keʻano o ke paniʻana o ka piko o ka CH ma o N.ʻO nā kumu nui he:

  1. E hele aku i kahi geometry hexagonal maʻamau maʻamau ma muli o ka hikiʻana o kahi hetero atom, no ka mea pololei, nāʻaelike no ka hoʻolālā nitrogen-carbon,
  2. Ke pani houʻiaʻana o kahi hydrogen atomi ma ke kekona me ke paipili electron nonshared, e like me ke kekona o ka lepe, aia i loko o ka orbital hybrid sp2, aʻaʻole i komo i loko o ka selectet p-electromatic. ʻO kēia hui kūikawā hoʻokahi ka mea i kuleana no nā mea kumu o nā pyridine,
  3. Hoʻopiliʻia ka dipole mau loa i kahi koho electronegativity kiʻekiʻe aʻe o ka'eneke nitrogen i hoʻohālikelikeʻia me kahi kumu kalapona.

Hoʻokumuʻia ka pyridine i nā pūnaewele koʻikoʻi, e like me ka vitamini nācin, pyridoxine, a me nā azines.

Ua hanaʻo Thomas Anderson i ka pyridine ma ka 1849 ma keʻano he hoʻokahi o nā hui i hanaʻia i ka iwiʻala. Ma hope oʻelua mau makahiki, ua loaʻaʻo Anderson i pyridine maʻemaʻe e ka māhele'āpana o kaʻaila o ka iwi. He ahi momona loa, keʻanoʻole, wai waikiki, wai maloʻo me kahi meaʻoluʻoluʻole, e like me keʻano o kaʻala.

Hoʻomaopopo pinepineʻiaʻo Pyridine i mua i nā mea lapaʻau a me nā mea kanu kino a he mea koʻikoʻi nui hoʻi a me ka mea pale. Hiki ke hoʻohuiʻia ka Pyridine i ka ethanol inā makemakeʻoe e hanaʻole ia no ke kāhana kanaka. He pili pono hoʻi ia i ka hanaʻana i nā mepyramine me nā meaʻokoʻa, i loko o ka vitro keʻano o DNA, i ka hana a sulfapyridine (lāʻau lapaʻau no ka mālamaʻana i nā maʻi viral a me nā maʻi kīpona), a me bactericides, me nā mea waipiu, a me nā mea wai.

ʻO ka hapa nui o nā mehana, me ka meaʻole i hanaʻia mai pyridine, i loko o ke kāʻei. ʻO ia mau pūpū e komo pū me nā hua B e like me pyridoxine a me niacin, nicotine, me nā mea kanu i loko o nā aʻapiuma, a me ka lāʻau anti-tuberculosis known as isoniazid. Ua hanaʻiaʻo Pyridine i nā mea i hakuʻia ma mua e like me keʻano o ka hoʻouluʻana o ka kalahu a me ke kāla. Eia naʻe,ʻo ke koiʻana i ka skyrocketing mō pyridine alakaʻi i ka hoʻomohalaʻana i nā hana hoʻolālā waiwai o ka ammonia a me ka acetaldehyde, a ma luna o nā 20,000 tonnes e huaʻia i kēlā me kēia makahiki ma ka honua holoʻokoʻa.

Nomenclature o pyridine

ʻO ka inoa pūnaewele o pyridine, e like me ka Hantzsch-Widman nomenclature i'ōleloʻia e ka IUPAC,ʻo ia azine. Akā, hoʻohana maʻalahiʻia nā inoa pūnaewele no nā pūnaehana maʻamau; akā,ʻo ka nomenclature o nā heterocycles e hoʻopaʻaʻia i nā inoa maʻamau. ʻAʻole i paipai ka IUPAC i ka hoʻohanaʻana azine i ka nānāʻana i pyridine.

Hoʻomaka ka heluʻana o nā hāmeʻa ma ke azine i ka hauoli. ʻO ka hoʻokaʻawaleʻiaʻana o nā kūlana e ka palapala Helene Helene (α-γ) a me ka hoʻohālike o ka nomenclature e like me keʻano maʻamau i nā hui homoaromatic (para para, meta,) ke hoʻohanaʻia i kekahi manawa. Maanei α, β a me γ e pili ana i nā wahiʻelua,ʻekolu, a meʻehā.

ʻO ka inoa maʻamau no nā huahana o pyridine pyridinyl, kahi i mua o kahi helu mua o kahi hoʻonohonoho mua i mua o ka helu. Akā ka inoa o ka mōʻaukala pyridyl 'ōleloʻia e ka IUPAC a hoʻohana nuiʻia ma kahi o ka inoa pūnaewele. ʻO ka hopena i hanaʻia ma o ka hoʻohuiʻiaʻana o kahi mea electrophile i ka'eneke nitrogen ka mea iʻikeʻia pyridinium.

4-bromopyridine

2,2'-bipyridine

Dipicolinic acid (pyridine-2,6-dicarboxylic acid)

ʻO keʻano o ka cation pyridinium

Ka hanaʻana o pyridine

Loaʻaʻia ka Pyridine ma keʻano o ka hopena o ka hoʻouluʻana i ka wahima a i laweʻia mai mai ka wala. He kūponoʻole kēia hana a hoʻohanaʻia: ua puni ka'ōhumahuʻu ma 0.1 i ka pyridine, a no laila ua pono ka hoʻomaʻemaʻeʻana i nā papahana maha, i hoʻemiʻia i ka puka hou. I kēia lā, hanaʻia ka pyridine nui i ka synthetically e hoʻohana ana i nāʻano haʻina, aʻo nā mea maʻamau ka kūkākūkāʻia ma lalo nei.

ʻO Pyridine Synthesis ma o Bohlmann-Rahtz

ʻO ka Pyridine Synthesis ma o Bohlmann-Rahtz hiki ke hāʻawi i nā pyridine i nā kumu nuiʻelua. ʻO ka hoʻonāʻana o ka hoʻohuiʻana e hoʻohana ana i nā ethynylketones e loaʻa ai i kahi kōwae aminodiene a, ma hope o ka hoʻomehanaʻana i ka mahana, e hoʻolāʻauʻia ka hoʻohālikeʻana e hoʻonui i ka pyrine 2,3,6-trisubstuted.

ʻO Pyridine Synthesis ma o ka papahana Bohlmann-Rahtz

ʻO ka pilina e pili ana i kahi Hantzsch Dihydropyridine Synthesis kaulana kahii kahi-e hoʻouluʻia ka'eamine a me nā'āpana o nā'anoʻanohehydhydyridine. ʻOiaiʻo Bohlmann-Rahtz Synthesis he mea maʻalahi loa ia,ʻo ka hoʻomaʻemaʻeʻana i nā kūwaena waena a me nāʻano kiʻekiʻe loa e pono ai no ka hoʻohālikeʻana i ka hoʻohaukūʻana i nā pahuhopu i kaupalenaʻia kona pono. Ua lanakila ka hapa nui o nā pilikia, no ka mea, uaʻoi aku kaʻoi aku o ka hōʻailona o Bohlmann-Rahtz ma ka pyridine hanauna.

ʻOiaiʻaʻole i hanaʻia kekahi noiʻi mechanistic, hiki keʻikeʻia e nā H-NMR nā mea i hala. Hōʻike kēia i ka huahana nui o ka hōʻano mua Michael Addition a me ka hoʻoiho proton e hiki nei ke lilo i 2Z-4E-heptadien-6-hoʻokahi i laweʻia a hoʻomaʻemaʻeʻia ma o ka chromatography tīwae.

Hoʻonuiʻia ka mahana o ke anuanu no ka hoʻoikaikaʻana Z/E isomerizations e pono ai no ka heteroannelation.

Ua hanaʻia kekahi mauʻano e hāʻawi ai i ka noʻonoʻo o ka tetra a me nā pyridine hoʻokūkū i kahi o ka hana. Ma mua o ka hoʻohanaʻana i ka butynone ma keʻano he pani, ua ho'āʻoʻo Bagley i nāʻano loli no ka hoʻololiʻana i ka 4- (trimethylsilyl) iʻole ka maikaʻi a me ka maikaʻiʻole akā-3-yn-2-one. Hōʻikeʻiaʻo DMSO wale nō a me EtOH nā mea hoʻoholo maikaʻi. Uaʻike maikaʻiʻiaʻo EtOH e like me ka pola a me keʻano palekana. DMSO e like me ka poro aprotic solvent. I loko o nā mea paleʻelua, ua hanaʻia ka hoʻopunipuniʻana me ka manawaʻole. Ua hōʻike pū akuʻo Bagley i ka hoʻomehemoʻana i kaʻawaʻawa e hoʻomau ai i ka holoʻana o ke kalapīmahu ma kahi haʻahaʻa haʻahaʻa.

Hoʻopiliʻia ka'āpana catidysis i ka hoʻohui pū. Ua hanaʻia heʻano nui o nā enamines me ka ethynyl ketones i loko o ka (5: 1) hui o ka acetic acid a me ka toluene no ka hāʻawiʻana i nā pyridine hanaʻia i hoʻokahi kaʻina ma nā hua maikaʻi.

Ma hope o ka holomuaʻana o ka hōʻoiaʻana o ka waikawa Brønstedt, uaʻimi ka chemist i ka ikaika o nā leʻaleʻa Lewis acid. Nā kūlana maikaʻi I hoʻohanaʻia heʻelua mau mol% wttbibium mahele aiʻoleʻumikumamālima mol% zinc bromide ma ka refluxing toluene. ʻOiaiʻaʻole i hanaʻia kaʻimi noiʻi mechanical, hiki iā mākou ke manaʻo i ka hoʻohuiʻana o ka mea hoʻoheheʻe wikiwiki i ka hoʻolāʻauʻana, Michael Addition, a me nā kaʻina hana isomerization.

ʻO kaʻaoʻao lalo ka palena o ka launa pū me nā mea'alahi. No ka laʻana, hanaʻia me ka cyano a me ka cyano a me ka Pāpā-butylester e hoʻokuʻu ana i nā hui. ʻO kekahiʻanoʻoluʻolu'ē aʻe,ʻo ia ka hoʻolālāʻana o ka ioni Amberlyst-15 e hoʻololi nei Pāpā-butylesters.

Ma muli o ka hikiʻole mai o nāʻehu, a no ka hoʻonuiʻana i ka hana o ka hana, ua hanaʻia ka hanana 3-component me ka ammonium acetate ma keʻano he kumu o ka hui amino. Ma kēia hana kūpono, hanaʻia ka'eamine i kahi a me nā mea e hoʻopili ai me ka'āpana ala.

I ka hoʻokolokolo mua, ZnBr2 a ua hoʻohanaʻiaʻo AcOH e like me nā hoʻohālikelike hou aku me nā toluene e like me ka mea pale. Eia naʻe, ua hōʻikeʻia mai i kēia manawa, i nā manawa a pau e hanaʻia nā meaʻaeʻa-ʻaloʻalo ma kahiʻano moluʻolu me EtOH e like me ka mea pale.

Ka Hoʻohui Hoʻoilinaʻo Chichibabin

Ua hōʻike muaʻia ka manaʻoʻo Chichibabin pyridine i ka 1924 a he mea nui loa ia ma kaʻoihana hanahana. He hana like ia, e pili ana i ka hopena o ka hoʻopiʻiʻana i nā aldehydes, ketones, α, β-unsaturated carbonyl pū. Eia kekahi,ʻo keʻano o ka hopena e hiki ke komo pū me ka hui pūʻana o nā huahana i luna ma ka ammonia maʻemaʻe a iʻole nā ​​mea hoʻohālike.

Kauia ʻO Pyridine

ʻO ka condensation o formaldehyde a me acetaldehyde

ʻO Formaldehyde a me acetaldehyde nā kumu o pyridine i heluʻoleʻia. Ma ka liʻiliʻi, he mea kūʻai a maʻalahi paha.

  1. ʻO ka hana mua e pili ana i ke kūkuluʻiaʻana o acrolein mai ka formaldehyde a me ka acetaldehyde ma o Knoevenagel condensation.
  2. Laweʻia ka hua hopena i ka acrolein me ka acetaldehyde a me ka amonia, a me ka dihydropyridine.
  3. ʻO ka hopena hope loa he hopena paleʻaiʻia me kahi mea hoʻomehana honua-kūpono e hāʻawi i ka pyridine.
  4. Hanaʻia ka hopena ma luna nei i kahi hāmeʻa kino me kahi mahana o 400-450 ° C. ʻO ka hui i hoʻohuiʻia he pyridine, picoline, a me nā pyridine methylated māmā, a me lutidine. Eia naʻe, hiki ke hoʻohuiʻia i ka mea hoʻohālike i hoʻohanaʻia a ma kekahiʻano, e like me nā koi o ka mea hana. ʻO keʻano,ʻo ka mea hoʻohālikelikeʻo ia ka paʻakai paʻakikī. ʻO ka mea maʻamau ka manganese (II) fluoride a iʻole cadmium (II) fluoride,ʻoiaiʻo ka thallium a me ka pūpuni male ka mea ke koho.
  5. Loaʻaʻia ke pyridine mai nā huahana ma kahi papahana nui.ʻO ka palena nui o Chichibabin pyridine synthesisʻo ia kona hua liʻiliʻi, unuhi i ka 20% o nā huahana hopena. No kēia kumu, ua emiʻole nāʻano i hōʻikeʻoleʻia o kēia hui.

ʻO Bönnemann ka hoʻokele kala

ʻO Bönnemann ka cyclization ka mea i kūkuluʻia i kahi'āpana mai ka huiʻana o nā'āpanaʻelua o ka acetylene mole a me kahi hapa o nitrile. ʻO kaʻoiaʻiʻo,ʻo ka loiloi kahi loli hou o ke kāʻei Reppe.

Hoʻomaʻinaʻia kaʻenehana e kēlā mehana wela mai nā wela kiʻekiʻe a me ke kaomi aiʻole ma o ka cycloaddition kiʻiʻia. Ke hoʻohanaʻia e ka mālamalama,ʻo kaʻoihana cyclizationʻo Bönnemann e pono aiʻo CoCp2 (cyclopentadienyl, 1,5-cyclooctadiene) e hana i mea catalyst.

Hiki i kēiaʻano ke hana i kahi kaula hoʻohālike pyridine e pili ana i nā pūnaewele i hoʻohanaʻia. No ka laʻana,ʻo ka acetonitrile ka mea e hoʻopuka i ka 2-methylpyridine, hiki ke hoʻokuʻuʻia ka hana like pyridine.

Nāʻano'ē aʻe

Ke kinikona Kröhnke pyridine

Hoʻohana kēiaʻano i pyridine e like me ka mea hana, akāʻaʻole e hoʻokomoʻia i ka huahana hopena. ʻO ka mea likeʻole,ʻo ka hopena e ho'āla i nā pyridine i hoʻololiʻia.

Ke hoʻoukaʻia me kaʻaʻa-ʻae, e loaʻa i ka pyridine ka hopena Michael-like me ka carboncyls i hoʻopaʻaʻia e lilo i ka pyridine a me pyridium buro. Hanaʻia ka hopena me ka ammonia acetate ma loko o ka 20-100 ° C i nā kūlana haʻahaʻa.

ʻO ka hoʻouluʻana o Ciamician-Dennstedt

Hoʻopili kēia i ka hoʻonuiʻia o pyrrole me ka dichlorocarbene e hoʻonui ana i ka 3-chloropyridine.

ʻO Gattermann-Skita

Ma kēia hopena, hanaʻia ka paʻakai meerate me ka dichloromethylamine ma mua o kahi kumu.

ʻO Boger pyridine hoʻomana

Nā hāʻaha o pyridine

Hiki keʻikeʻia nā haʻuki o kēia mau mea no pyridine mai ko lākou papahanaʻeleʻele:

  1. Hoʻopili ka heteroatoma i nā pyridine me keʻanoʻole ponoʻole i nā hoʻololiʻenehana koho electrophilic maʻamau. I ka mea like, hiki i nā pyridine ke hōʻeha i ka hopena nucleophilic. Hiki i nā Pyridines ke hoʻololi hou i ka hoʻohoihoiʻana (SEAr) ma mua o ka hoʻololiʻana (SNAr) ma mua o ka benzene.
  2. Hiki i nā'āpana electrophilic kū'ē i ka maikaʻi ma ka Natom a ma nā bC-niho,ʻoiai nā mea hana nucleophilic makemake i nā a- a me nā CC.

ʻO ka hoʻonuiʻiaʻana i ka Nitrogen

I nā hopena e komo ana i ka hoʻolālā paʻaʻana me ka paina o nā electrons ma ka mīkini mīkini, e like me ka protonation a me ka hoʻolālā, pyridines e hana like e like me nā aliphatic tertiary a me nā amine momona.

Ke hanaʻia kahi pyridine e like me kahi kumu a nucleophile paha, e hanaʻia he pyterinium cation kahi i mālamaʻia ai ka sextet aromas, a loaʻa ka hauʻoli i ka uku kūpono kūikawā.

Hoʻomākaukau ma Nitrogen

Kūkuluʻia ka Pyridines i ka crystalline, i nā hygroscopic pinepine, i nā paʻakai me nāʻoihana pīkole.

Hoʻolaha ma Nitrogen

Hoʻomaopopo kokeʻia kēia ma ka hopena o pyridines me nā paʻakai nitronium, e like me nitronum tetrafluoroborate. ʻO nā mea hana pālolo likeʻole me ka nitric acid,ʻo ke kumu, he alakaʻi wale nō i ka N-protonation.

ʻO Acylation ma kaʻaila

Hana kokeʻia nā chloride a me nā mea arylsulfonic me nā pyridine e hoʻonui ana i nā salina 1-acyl- a me 1-arylsulfonylpyridinium.

ʻO Alkyl halides a me sulfates e hana wikiwiki me nā pyridines e hāʻawi ana i nā soda pyridinium quaternary.

Nā Hoʻoponopono Nucleophilic

'Aʻohe like me benzene, hiki i nā substitutions nucleophilic āpau ke mālama pono a kūpono i ka pyridine. ʻOiai no ka mea, he emi ka liʻiliʻi o ka liʻiliʻi o ke anapuni o ka carbon carbon. ʻO kēia mau hanana e pili ana i nā pani pani me ka laweʻiaʻana o ka ion hydride a me nā hōʻiliʻiliʻana i mea e loaʻa ai kahi hoʻonohonoho aryne aʻoi mau i ka 2- aiʻole ka 4.

ʻO ka Pyridine wale nō ka mea i hikiʻole ke hoʻokū i ka hoʻokumuʻana i kekahi mau pono nucleophilic. Eia nō naʻe, hiki i ka hoʻololiʻana o nā pyridine me nā bromine, sulfonic acid a me ka chlorine, a me ka fluorine ka hopena i kahi hui. Hiki ke loaʻa ke kūkuluʻia o nā pūpona organolithium mai ka hui nui loa o ka fluorine. I ka piʻi nui, hiki ke hanaʻia ka nucleophilic me nā lāʻau alkoxides, nā mea'ōpala, amine, a me nā mea amonia.

ʻAʻohe heterocyclic hiki i nā hopena ke hoʻohālikelike no ka hoʻohanaʻana i kahi hui haʻaleleʻino e like me ka ion hydride. Hiki ke loaʻa nā huahana Pyridine ma kahi 2 ma o ka hoʻoponoponoʻo Chichibabin. 2-aminopyridine hiki ke hoʻomau i ka hana i ka wā e hoʻohanaʻia ai ka sodium amide e like me ka nucleophile. Hoʻokumuʻia ka moleuma hydrogen ke hoʻopiliʻia nā protons o ka hui amino me ka ionic hydride.

E like me benzene, pyridine Hiki ke loaʻa i nā kauā likeʻole heteroaryne ma o nā substitua nucleophilic i pyridine. ʻO ka hoʻohanaʻana i nā alakalina ikaika e like me ka sodium a me ka potassium tert-butoxide e hiki ke kōkua i ka hoʻohemoʻana i nā mea pyridine i ka hoʻohanaʻana i ka pono e haʻalele i ka hui. Ma hope o ka hoʻokomoʻiaʻana o ka nucleophile i ka pilinaʻekolu, e hoʻohaʻahaʻa ana i ka koho a alakaʻi i ke kāpiliʻana o ka paila e loaʻa iʻelua mau hanana hiki mai.

Nā Kōkua Electrophilic

Hiki i nā substituted pilali koho pyridine ke hoʻomau i kekahi wahi aʻaʻole hoʻi e hoʻomauʻia. I kekahiʻaoʻao, hiki ke hoʻouluʻia ke kumu heteroaromatic ma o ka functionalization o ka hāʻawi pūnaewele. ʻO Friedel-Crafts alkylation (acylation) keʻano o nā hoʻohuihui a me nā'ākala. ʻAʻole e loaʻa ka pyridine i kēia hiʻohiʻona mai ka hopena o ka hoʻonuiʻia o kaʻaila nitrogen. ʻO nā pani i ka manawaʻekolu ma kahi o nā'āpana kalapona'onihune i loko o ke apo e like me ka hoʻololiʻana i ke kohopili.

Nā Kūkulu o Pyridine N-'Oxide

Hiki i nā hoʻololi koho koho ke hoʻololi i keʻano o ka pyridine ma ka 2- a iʻole ka 4-ka nui ma muli o ke kū'ēʻana i ka hoʻopiʻi pīpī σ. Eia naʻe, hiki ke hoʻohanaʻia nāʻano hoʻokolohua i ka hanaʻana i ka hoʻololi electrophilani ma pyridine N-oxide. Ma muli o ka hoʻolālā'okōpona i ka manawa e ukaliʻia ai. No laila, uaʻikeʻia ka hoʻokomoʻiaʻana o ka oxygen e hoʻohaʻahaʻa i ka māmā ma luna o ka mea hauʻoli a hoʻonui i ka pani ma ka 2 a me ka 4-position carbons.

Hoʻohālikelikeʻia nā pūpū o sulfur sulfona a me nā phosphorus maʻamau e hiki ke maʻalahiʻia i kēia mau mea i hoʻohanaʻia e wehe i ka oxygen atom. ʻO ka huihuʻu Triphenylphosphine he mea hana i hanaʻia ma hope o ka hoʻonāʻana o ka huihuʻi Triphenylphosphine. ʻO kekahi mea hana hou paha e hiki ke hoʻohanaʻia e hoʻopau i kahi oxygen atom mai kahi'ē aʻe. ʻO kaʻike ma lalo nei e pili ana i ka hoʻohālikeʻana o ka pilikino maʻamau me pyridine.

Hoʻomaʻaʻia keʻano o ka pyridine nitration e koi ana i kekahi mauʻano koʻikoʻi, a he mau hua liʻiliʻi nō ia. ʻO ka paneʻana o ka dinitrogen pentoxide me pyridine i mua o ka sodium e hiki ke hopena i ke kūkuluʻana o 3-nitropyridine. Hiki ke loaʻa nā huahana o pyridine ma o ka hoʻokomoʻiaʻana o ka tetrafluoroborate nitronium (NO2BF4) ma ka laweʻana i kaʻaila nitrogen ma mua a me kaʻike. Hoʻomaopopo o nā meaʻelua o ka 6-dibromo pyridine hiki i ka hopena o ka 3-nitropyridine ma hope o ka hoʻokuʻuʻana i nā mana bromine.

ʻO kaʻenehana kūpono he meaʻoi aku kaʻoluʻolu ma mua o ka sulfonation pololei o pyridine. Hikiʻia ka pyridine ma 320 ° C e hiki ai ke hoʻopiliʻia ka pyridine-3-sulfonic acid ma mua o ka waipū sulfuric acid ma nāʻano wela like. Hiki ke loaʻa ka hoʻonuiʻia o ka sulfur element i ka'enela amene ma ka hanaʻana i kahi hui SO3 i mua o mercury (II) sulfate e hana nei he mea catalyst.

Hoʻomaopopo i ka chlorination a me ka bromination e hoʻomau i ka maikaʻi me ka likeʻole o ka nitration a me ka sulfonation. Hiki ke loaʻa ka 3-bromopyridine ma o ka hopena o ka bromine i ka sulfuric acid i ka 130 ° C me pyridine. Ma ka chlorination, hiki ke hoʻohaʻahaʻaʻia ka hopena o 3-chloropyridine i mua o ka aluminiuma alumini e hana ma keʻano he mea hoʻohui ma 100 ° C. Hiki i ka hopena o ka halogen a me palladium (II) ka hopena ma 2-bromopyridine a me ka 2-chloropyridine.

Nā noi o Pyridine

ʻO kekahi o nā mea laʻa e pili nui ana i nā hale hana pilikino he pyridine. I ka 1989,ʻo ka nui o ka pyridine ma ka honua holoʻokoʻa he 26K tonnes. No 1999,ʻo 11 mai loko mai o nā 25 nui nui o pyridine pūnaewele hanana i hoʻonohoʻia ma'Europa. ʻO nā mea nui pyridine pūʻia nā Koei Chemical, Imperial Chemical Industries, a me Evonik Industries.

I nā 2000 mua, ua hoʻonuiʻia ka hana pyridine ma kahi kiʻekiʻe. Eia kekahi lā,ʻo China wale nō ka mea i loaʻa i ka manawa hiki ke hoʻonui i nā kaha o 30,000 tonnes. I kēia lā,ʻo ka hui pūʻana ma waena o ka US a me Kina ka hualoaʻa i loko o ka hana nui pyridine o ka honua.

Pesticides

Hoʻohanaʻia ka Pyridine i mua iʻelua mau lāʻau lapaʻau diquat a me paraquat. I ka hoʻomākaukauʻana o nā fungicides-pyrithione, hoʻohanaʻiaʻo pyridine e like me ka mea papa.

ʻO ka hopena ma waena o Zincke a me pyridine ka hopena i ka hanaʻana o nā meaʻelua - laurylpyridinium a me ka ceylpyidinium. Ma muli o ko lākou mau waiwai hōʻailona, ​​ua hoʻokomoʻia nā pūpūʻelua i nā niho niho a me ka waha.

ʻO kahi hoʻouka kauaʻana e kahi mea hana hoʻohālike i nā pyridine ka hopena o nā naki N-alkylpyridinium,ʻo kēiaʻano helplprididinium chloride he kumu hoʻokahi.

ʻO ka Palena o Paraquat

Nā hopena

ʻO kekahi hana e hoʻohanaʻia ai pyridine ma Knoevenagel condensations, kahi e hoʻohanaʻia ai heʻano liʻiliʻi, polar, a me ka hoʻoheheʻe kumu. He kūpono loa ka Pyridine no ka hoʻohalahalaʻana, kahi i lilo ia i kumu no ka hoʻopauʻiaʻana i ka hoʻopiʻiʻiaʻana ma ka hoʻopaʻaʻana i ka hualoaʻaʻo hydrogen halide e lilo i paʻakai pyridinium.

I loko o nā hōʻailona a me nā esterifications, hoʻonāʻo Pyridine i nā anhydrides a iʻole nā ​​hamo waipiʻaleka. ʻOi aku kaʻoihana o kēia mau kuhiana he 4- (1-pyrrolidinyl) pyridine a me 4-dimethylaminopyridine (DMAP), he mau pyridine ka mea hoʻohemo. I ka hoʻouluʻana i ka hoʻouka, hoʻohanaʻia ka Pyridine i kumu.

Ke kāpiliʻia o pyridinium ma ka hoʻokahuliʻana i ka hoʻoihoʻia me pyridine

ʻO ka Pyridine kekahi mea waiwai nui i kaʻoihana textile. Ma waho o ka hoʻolimalimaʻiaʻana e like me ka mea pale i ka hanaʻana o ka pale a me nā waiū, ua hoʻohanaʻia hoʻi e hoʻonui i ka pūnaewele pūnaewele.

Hoʻomaopopo ka US Food and Drug Administration i ka hoʻohuiʻana o pyridine i nā mea liʻiliʻi i nā meaʻai e hiki ai ke hāʻawi iā lākou i ka meaʻawaʻawa.

I nā hopena, aia ka paepae helu o pyridine ma'ō 1-3 mmol·L-1 (79-237 mg · L-1). Ma keʻano he kumu, hiki ke hoʻohanaʻia ka pyridine e like me ka Karl Fischer reagent. Eia naʻe, hoʻohana mauʻia ka imidazole e pani ai i pyridine no ka mea, heʻalaʻoluʻolu ka (imidazole).

ʻO ka mua i ka Piperidine

ʻO Pyridine hydrogenation me ka ruthenium, ka cobalt, a me ka catalyst-catalyst catalyst at high temperatures results in the production of piperidine. He kumupona helu hauʻoliʻo ia he papa hana o ka mea hana pono.

Nā Kū'ē Kūikawā Ma muli o Pyridine

Ma 1975, ua kūkuluʻo William Suggs lāuaʻo James Corey i ka pyridinium chlorochromate. E hoʻohanaʻia ana e pale i nā waipika lua i nā kinetona a me nā meaʻaina mua i aldehydes. Kūkuluʻia ka Pyridinium chlorochromate i ka manawa e hoʻonuiʻia ai ka pyridine i ka hopena o ka hydrochloric a me ka chromic concentrated.

C5H5N + HCl + CrO3 → [C5H5NH] [CrO3'Oʻohana]

Me ka chromyl chloride (CrO2Cl2) he kinoʻinoino ka mea e pono ai ke huli. Hoʻokahi o lākou e hoʻohana i ka pyridinium chloride e hana i ka choda (VI) oxyide.

[C5H5NH+] Cl- + CrO3 → [C5H5NH] [CrO3'Oʻohana]

ʻO ke kumuhana Sarret (ka complex of chromium (VI) oxyide me pyridine heterocycle ma pyridine), pyridinium chlorochromate (PCC), reagent Cornendth (pyridinium dichromate, PDC), a me ka reagent Collins (ka complex of chromium (VI) oxide me pyridine he hemoloka ma dichloromethane) e like me ka chromium-pyridine pū. Hoʻohanaʻia lākou no ka hoʻonāʻana, e like me ka hoʻohuliʻana i nā kula kiʻekiʻe a me nā mea mua loa i nā kinetona.

ʻAʻole pono nā mea keʻakeʻa o Sarret a me Collins i mea hoʻomākaukau, akā, he mea weliweli hoʻi. ʻO lākou he hygroscopic a hiki ke loli i ka wā hoʻomākaukau. No laila, ua'ōleloʻia ka hoʻohanaʻana i ka PDC a me ka PCC. ʻOiai ua hoʻohana ikaikaʻia nā meaʻelua i nā 70s a me ka 80s,ʻaʻole i hoʻohanaʻia i kēia manawa no ko lākou hōʻino a hōʻoiaʻiʻoʻia i ke kino.

ʻO ka hanana o ka Craestree's catalyst

I ka hoʻohuiʻana i ke kemikū, hoʻohana nuiʻiaʻo pyridine me he ligand. He mea ia e like me keʻano o ka 2,2'-bipyridine, me nā'āpana 2 pyridine i hoʻopaʻaʻia e kekahi nūpepa, a me terpyridine, kahi mole o nā kaha 3 pyridine i hui pūʻia.

Hiki ke hoʻohanaʻia kahi papahana Lewisʻoi aku i mea e pani ai no ka ligand pyridine e pili ana i kahi'āpana hao. Hoʻopiliʻia kēiaʻano ma ka hopena o ka hoʻohui polymerization a me nā hoʻohālike hydrogenation, e hoʻohana ai, no ka mea,ʻo Carabtree ke catalyst. ʻO ka pyridine Lingard i hoʻololiʻia i ka manawa o ka hoʻopiʻiʻana e hoʻouka houʻia ma hope o kona pauʻana.

E hoʻomaopopo '

Nomenclature o ke Organic Chemistry: Nā Manaʻo IUPAC a me nā inoa i makemakeʻia 2013 (Blue Book). ʻO Cambridge:ʻO ka Royal Society of Chemistry. 2014. p. 141.

Anderson, T. (1851). "Ueber die Producte der trocknen Destillation thierischer Materien" [Ma nā hua o ka wehewehe maloʻo o nā mea holoholona). Annalen der Chemie a Pharmacie. 80: 44.

Sherman, AR (2004). "Pyridine". Ma Paquette, L. Encyclopedia of Reagents for Organic Synthesis. e-EROS (Encyclopedia of Reagents for Organic Synthesis). Niu Ioka: J. Wiley & Sons.

Behr, A. (2008). ʻO Angewandte homogene Katalyse. Weinheim: Wiley-VCH. p. 722.